It's Always Sunny In Philadelphia: 20 Funniest Episodes So Far

It's Always Sunny in Philadelphia The Gang Goes to Hell

It’s Always Sunny in Philadelphia has now become one of the longest-running sitcoms of all time. As it nears the end of its 12th season, we’re often left wondering at how a show packed full of depravity and sociopathic lead characters could possibly have lasted so long. Star Charlie Day even suggested that network FXX forgot the show was still on, but it is because of Day, Kaitlin Olson, and their co-stars and series developers Rob McElhenney and Glenn Howerton, that It’s Always Sunny finds just the right balance between controversial and downright hilarious.

Through their various schemes and pranks, the gang has put together so many episodes that even some of the most memorable can’t find their way onto this list. At time of writing, 132 episodes of It’s Always Sunny have aired, and every single one of them offers something to make you laugh, cringe, or in the best case scenario – a bit of both.

Let’s take a look at It’s Always Sunny in Philadelphia’s 20 Funniest Episodes.

20 “Paddy’s Pub: Home of the Original Kitten Mittens” (5x08)

It's Always Sunny Kitten Mittens

You know it’s a strong list when Charlie and his kitten mittens are as low as number 20. The episode kicks off with Charlie at his high-pitched best, in one of the first of many It’s Always Sunny home advertisements. The pitch is designed for an upcoming merchandising convention, and each of the gang goes their own way in coming up with ideas to make money from Paddy’s, after Mac eats Dee’s contract which gives her all the merchandising rights.

True to character, Dennis pitches a Paddy’s thong, Mac creates the Dick Towel brand, while Frank puts forward two ideas of his own: a tequila firearm, and a Paddy’s stress ball that is literally just an egg. The gang harasses the lawyer with their various plans to profit from each other’s ideas, but a fairly large oversight on their part leads to the lawyer gaining all of Paddy’s merchandising rights in yet another failed scheme.

19 “The Gang Goes to Hell: Part 2” (11x10)

It's Always Sunny in Philadelphia Season 10

The gang is at their best (or should we say worst?) when confined in a small space with only each other for company. The episode follows on from “The Gang Goes to Hell: Part 1”, which sees the gang board a Christian cruise ship, only for each of them to end up tossed in a bunker for crimes such as harassment, homophobia, and excessive drinking. Stuck in the bunker, the gang has to find a way to make the best of their time together, while they notice that they may be on a sinking ship.

Though there is a practical musical piece thrown in to keep things ticking, the episode is one of the most dialogue-heavy. On the brink of death, they begin to open up to one another, as Mac ponders his sexuality, Dennis confesses his love for Dee, and Charlie shoots himself in the head. In an appropriate end to season 11, the gang learns through confessions that they’re really not good people, but even more appropriate are their efforts to save only themselves when they are eventually rescued.

18 “The Gang Gets Trapped” (7x09)

It's Always Sunny The Gang Gets Trapped

Inspired in part by Indiana Jones, “The Gang Gets Trapped” sees Frank, Dennis, and Dee break into a stranger’s house in search of a lost artifact – in this case, a rare vase – while Charlie and Mac sit in the getaway van and argue over chips. The episode is another example of the gang confined to a single space, as they are forced to act on instinct when the Southern family returns home.

Frank struts about the place with a whip, while Dennis and Dee hide in the house’s various closets. In search of Mac and Charlie’s help, Dee constructs a plan to break the pair apart by asking why Charlie doesn’t get to hold the walkie-talkie, which Charlie responds to by entering the house of his own accord.

As the “hillbilly” owners try to work out their family troubles, Dennis eventually decides to just walk out, passing the owners on the way, who turn out not be hillbillies at all, but an Asian family. Mac enters at that point under the guise of a Swedish plumber, and Frank smashes the vase with the whip, putting an end to a thoroughly pointless break-in mission, but an entertaining one at that.

17 “The Gang Broke Dee” (9x01)

It's Always Sunny The Gang Broke Dee

“The Gang Broke Dee” might not be the outright funniest of episodes, but that’s actually kind of the point. With her career going nowhere and having been called a “bird lady” one too many times, Dee has hit rock bottom, and the guys (apparently) generously book her into an open mic night at a comedy club.

With her own brand of humor, which Dennis finds frankly detestable, Dee quickly rises to the top of the comedy circuit. Finally offered a fill-in spot on Conan, she pulls back the curtain to reveal only the gang and several extras (two of whom she slept with on her way to pretend stardom).

The whole thing was set up as one of the most twisted pranks the gang has ever pulled. The reveal is funny enough to make up for the time spent watching Dee’s attempts at comedy, though Kaitlin Olson is at her dry-heaving best through the episode, and Dennis’ mad reaction to being left out of the joke keeps us laughing all the way to the end.

16 “Mac Bangs Dennis’ Mom” (2x04)

It's Always Sunny Mac

With Charlie now running Paddy’s and free of all “Charlie work”, Dennis invites the Waitress to go out with him as leverage. But Charlie, who learns that Mac has slept with Dennis’ mom, enlists Dee’s help in one of Sunny’s most complicated revenge plots. Charlie Day is at his unhinged best as Charlie completely grasses on Mac, convincing Dennis through Dee that he should sleep with Mac’s mother in turn.

Dennis attempts to seduce both Mac and Charlie’s moms, which shatters the Waitress, who Dee has befriended on Charlie’s instruction. Dee, who is promised by her old job back if she complies, suggests that the Waitress should sleep with Charlie to get back at Dennis. All is going smoothly for Charlie, until the Waitress reveals that she slept with Frank instead.

This doesn’t affect Dennis in the slightest, while Charlie goes back to pining over the Waitress. For such an elaborate plan, nobody comes out of it any better or worse besides the Waitress, whose life is ruined just that little bit more by the oblivious gang.

15 “The Gang Solves the Gas Crisis” (4x02)

It's Always Sunny The Gang Solves the Gas Crisis

“The Gang Solves the Gas Crisis” revolves around a scam thought up by Mac, which in itself is one of the gang’s least crazy ideas, but naturally things begin to spiral out of control almost immediately. As the brains of the group, Mac decides that the gang should stock up on gas, and sell it when the gas prices go up again. Dennis assumes his position as the looks of the team, and Charlie the “wildcard, b---hes!

After Charlie has spit several fireballs and drunk about a gallon of gas, the guys realize how dependent they are on Frank and Dee. In another show, this may have been a touching moment, but it comes as they watch Frank torture Dee in a urinal.

Frank comes aboard as the muscle, and Dee as the “useless chick”, and the gang hop in Frank’s "rape van" to stitch up Bruce Mathis, whose only crime is attempting to donate money to a Muslim charity. Unfortunately, Charlie takes his role as the wildcard just a little too seriously, transforming a classic action trope into pure chaos.

14 “Chardee MacDennis: The Game of Games” (7x07)

Glenn Howerton as Dennis Reynolds in It's Always Sunny in Philadelphia

Fresh out of schemes, the gang takes a day off to introduce Frank to “Chardee MacDennis” – a game they created themselves back in the day. But as we see very evidently in 20 minutes of Sunny madness: “It’s not just a game. It’s a war.”

Even a simple drinking game descends into mayhem for the gang, who make their way through three levels of varying alcoholic beverages by cheating, smashing up their own bar, and suffering through some insane forfeits. At different points, Frank ends up in a dog cage eating the separate ingredients of a cake, Dennis gets a dart thrown through the palm of his hand, and Charlie tries willingly to throw up the grapes he has just eaten.

It’s the same five characters stuck in the same one room for the entire run time, but that only proves the strength of the lead characters, who can make funny out of almost nothing, and whose maniacal exploits are more entertaining than anything a minor character could possibly offer the show.

13 “The Gang Beats Boggs” (10x01)

It's Always Sunny The Gang Beats Boggs

After a long hiatus between seasons, “The Gang Beats Boggs” was a welcome return for the cast. Not only do they each find their own way to drive the unsuspecting passengers crazy, but they are all blind drunk, as they try to break Wade Boggs’ record of drinking an unspecified number of beers over the course of a transatlantic flight.

Frank and Dennis are left behind fairly swiftly, as each tries instead to join the “Air Sex Society”, which involves a Sherlock-style deduction from Dennis in full creep mode, and the return of Frank’s Dr. Toboggan character as he goes some way to poisoning a college student. Dee is in just about the worst state of them all, but Charlie, who is taking the game entirely seriously, quickly catches up over an imaginary conversation with the real Wade Boggs.

After leaving Dee on a baggage carousel, it’s down to Charlie (70 beers deep and subtitled at this point) to replicate Boggs and hit a home run, which he nails on his first attempt. It’s fitting for a show like Sunny that the one time the gang gets a win, there’s almost no chance they remembered it the next day.

12 “The D.E.N.N.I.S. System” (5x10)

It's Always Sunny The Dennis System

Demonstrate value, Engage physically, Nurture dependence, Neglect emotionally, Inspire hope, Separate entirely; Dennis Reynolds’ fool proof way of maintaining his inflated ego when it comes to the opposite sex. When Dennis is challenged by his sister to win back pharmacist Caylee (played by Howerton’s real wife, Jill Latiano) on whom he had already employed the system, all hell breaks loose as the rest of the gang tries to follow suit.

Charlie, having completely misunderstood, takes his stalking of the Waitress to the next level by sneaking into her apartment and breaking her possessions. After botching his system, Dennis suggests that Charlie go for broke and stab the Waitress, in order to nurse her back to life and prove his value.

Mac swoops in on Caylee with his own M.A.C. system (Move in After Completion) and Frank enters the picture with his SCRAPS solution, but Dennis still hasn’t won her back. With their cover blown, Frank debuts Dr. Mantis Toboggan, and drops a “monster condom” on the floor as a last resort, capping off an episode that perfectly demonstrates just how creepy and out-of-touch the gang actually is.

11 “Mac and Charlie Die: Part 1” (4x05)

It's Always Sunny Mac and Charlie Die

Part 2 of “Mac and Charlie Die” revolves more around the rest of the gang dealing with Mac and Charlie’s “deaths”. Dennis is only mad for having been left out of the suicide pact, and throws several glory hole-centric parties in the meantime, Dee sees right through their fake-out, and Frank is genuinely broken up.

But Part 1 is Mac and Charlie at their best, as they fake their own deaths to escape the wrath of Mac’s father. Upon Luther’s release from prison, and with a promise to “eat their butts”, Mac and Charlie crash, blow up, and repeatedly shoot Dee’s car, succeeding only in giving Mac a concussion. A fully conscious but entirely out-of-it Mac decides that the best solution is to wear a wedding dress, while the pair attempt to leave dental records at the scene instead, pulling out several of Charlie’s teeth with minimal effort.

Add in the fact that Luther simply wanted to get as far away from Mac and Charlie as possible, and you have two grown men in wedding attire camping out on the roof of their own bar eating nothing but beans.

10 “The Gang Buys a Boat” (6x03)

It's Always Sunny The Gang Buys a Boat

Most episodes of Sunny end with the gang’s latest idea going up in smoke, but rarely does that mean literally. With their sights set on buying a yacht (for at least a few days), Charlie, Mac, and Dennis settle for a battered old boat, and go about using the profits gained from to do it up. Naturally, Charlie winds up eating barnacles off the side of the boat, Dee’s contribution is to dance around like an AirDancer at a car dealership, Frank drops his keys in the ocean, and the boat catches fire at the end of it all.

But “The Gang Buys a Boat” is all about Mac, Dennis, and “the implication”. In a scene expertly written by Day and McElhenney, Dennis explains “the implication of danger”; that by luring women into the middle of the ocean, they can’t possibly refuse him. When Mac doesn’t quite get it (“It sounds like she doesn’t want to have sex with you…”), Dennis is sincere enough to make Mac thing he’s in the wrong, but in reality digs himself deeper into his sociopathic hole: “If the girl says no then the answer obviously is no, but the thing is she would never say no, because of the implication…

9 “The Gang Gets Quarantined” (9x07)

It's Always Sunny The Gang Gets Quarantined

The writers on Sunny have made Danny DeVito do some outrageous things. We’ve seen Frank crawl naked from inside a couch, get himself trapped in a playground coil, and literally hang himself from the ceiling of Paddy’s. But “The Gang Gets Quarantined” goes a step further, transforming the Oscar nominee into a completely hairless slug-like creature bathed in hand sanitizer. In one of DeVito’s best episodes, the gang is once more confined to Paddy’s as a flu virus breaks out through Philadelphia.

One by one, Dee and the guys get locked in the bathroom (“You’re gonna quarantine me inside a quarantine?”), getting steadily more sick as Frank obsesses over purity and evolution. Dennis’ complete denial that he would succumb to such a sickness offers some memorable Dennis moments, including a dead-eyed high note that lasts for an uncomfortably long time, as well as “If I found myself getting sick, I would simply say – ‘SICKNESS BE GONE!’

The end twist that the gang are simply alcoholics and are having withdrawal symptoms is one we should all have seen coming, and let’s be honest – their Boyz II Men harmonies are spot on.

8 “Mac and Dennis Move to the Suburbs” (11x05)

It's Always Sunny Mac and Dennis

After a middling start to its 11th season, It’s Always Sunny throws everything into this mid-season episode, as “Mac and Dennis Move to the Suburbs” transitions from light-hearted rom-com to full-on horror over the course of 20 minutes. In need of a new apartment, Mac and Dennis move to the ‘burbs to escape the city life, and the pair quickly falls into married couple stereotypes.

But as Dennis becomes bitter over his role as the breadwinner, and Mac is more and more isolated in his own home, a major tone shift develops on screen. Dennis devolves into stripping naked and severely beating his imaginary neighbor, while Mac literally kills and eats his own dog to the tune of a piano theme that would not be out of place in The Shining (Dennis’ response to finding Mac burying their pet is appropriately sadistic: “What’s that?” “Dog grave.” “Huh.”)

The episode uses every suburban-living cliché in the book, and its characters are so out of place that their deterioration seems entirely natural. It says a lot about the gang that you completely believe Mac and Dennis as murderers when the pair are stranded outside their comfort zone.

7 “Charlie Work” (10x04)

Charlie Day as Charlie Kelly on It's Always Sunny in Philadelphia

On a list of “best” episodes, you might expect to find “Charlie Work” somewhere near the top (if not at number one), but for all its technical brilliance, the episode just falls short in the humor department. That’s not to say it isn’t funny – if anything, Charlie is at his funniest during his most frantic moments, and the full extent of Charlie Day’s physical comedy is on show in the seven-minute scene shot (seemingly) in one take.

Even if his intentions to keep the bar alive are noble, the show couldn’t just let Charlie be the good guy for once. As the rest of the gang works on their “chicken and airline miles” scam in the background, Charlie’s attempts to cover it up lead to several carjackings, one customer’s worst ever dining experience, and the waste of a perfectly good 4000 steaks.

Meanwhile, Charlie finds a further roadblock as Frank lathers himself in black paint to overcome his anxiety, while Dennis’ overly sweaty McConaughey impression gets funnier every time.

6 “The Gang Goes to a Water Park” (12x02)

It's Always Sunny Water Park

The newest entry on this list, “The Gang Goes to a Water Park”, is the second episode of the ongoing 12th season. Set as a one-off, there are no scams planned (although Dennis is caught up in a scheme almost immediately), no stakes, no Paddy’s – just good, old-fashioned, water park-related comedy. As each of the gang differs on the way to best utilize a water park, they quickly split up into groups.

Mac and Dee end up stuck halfway down a kid’s waterslide, and after pissing off the attendant (played by Game of Thrones co-creator David Benioff), they are crushed by a steady stream of overweight kids. Charlie and Frank, the inevitable wildcards of the group, find their way to the front of the lines by scaring the entire park into thinking Frank has AIDS, and then attempt to ride the unfinished Thunder Gun Express attraction by pouring a single bottle of water down before them. Dennis abandons his plan to pick up women by pretending to have a daughter when a young girl named Abby claims to be said daughter. The pair grow closer as the episode develops, they each teach the other a thing or two about scheming.

The gang rarely crosses paths at all, but Dennis and Charlie’s brief encounter sums up the gang altogether. “Are you guys doing an AIDS thing?” and “You doing a fake daughter thing?” are the only words they need to share.

5 “The Gang Tries Desperately to Win an Award” (9x03)

It's Always Sunny Frank

“The Gang Tries Desperately to Win an Award” threatens to break the fourth wall on several occasions, as the show employs a different kind of humor to address the fact that they’re never nominated for awards in the real world. There are too many quotes to fully do justice to how on-the-nose the episode actually is, but Frank’s “If you wanna win a nomination, you gotta play the game” covers the overall gist.

In the actual episode, they have been overlooked for the Restaurant Bar Association’s Best Bar Award, and the gang goes about trying to replicate the playful and inoffensive tone of the bar across town (a very obvious metaphor for the sitcoms that are nominated over Sunny). As the gang invites members of the RBA to Paddy’s, Charlie writes a song that might have served as a theme for a lighter sitcom and Dee is warned against working on her comedy (“Men are intimidated by funny women – we just need you to be pretty and benign.”)

So how does it play out? Charlie performs an entirely different tune, aptly titled “Go F--- Yourself”, while a failed attempt at banter leads to Mac actually saying the words, “Ma’am, what would you like to drink, and we won’t j--- on anything.” That’s how it plays out.

4 “Charlie Catches a Leprechaun” (11x08)

It's Always Sunny Dennis and Dee

It’s St. Paddy’s day, and Dennis looks to cash in on the bar’s most profitable day, while Charlie is in search of something else altogether. “Charlie Catches a Leprechaun” takes everything that is good about the show’s main characters, and amps it up to the next level.

Charlie has always been a paint-drinking lunatic, Dee a terrible character actor, and Dennis a short-tempered sociopath. In this season 11 episode, those traits turn the gang into legit criminals, as Charlie tortures a man he believes to be a leprechaun (and quite believably would have killed him, if not for the gang’s intervention). A combination of Dee’s characters (“I can’t tell if you’re doing a thing now, or if this is just who you’ve become”) and the underwhelming response to his "Paddy’s Wagon" pushes Dennis to kidnap and rob several innocent Philadelphians at gunpoint.

Howerton’s delivery of such simple lines as “Dee – shut up!” are gold here, while Charlie Day is in some of his best form. Upon learning that his captive is actually a pickpocket, Charlie delivers the single greatest excuse ever given for torturing a little person: “That makes sense, because he kept saying ‘I’m a pickpocket! I’m a pickpocket!’ And I just thought that was, like, a metaphor for, you know… I'm a leprechaun.” “Charlie Catches a Leprechaun” fully commits to its gags, and there’s a barely a moment to breathe between the two hysterically dark storylines.

3 “Sweet Dee’s Dating a Retarded Person” (3x09)

It's Always Sunny Dennis Mac and Frank

For It’s Always Sunny, even the title card is gag, but never is it used more effectively than this episode, which cuts gloriously from Dee’s “There is no way I’m dating a retarded person," and straight into: “Sweet Dee’s Dating a Retarded Person”. You know what you’re in for from the very beginning, but Sunny’s ability to skirt around the edge of potentially edgy topics without ever stepping directly into offensive territory became a huge factor in the show’s later success.

While the rest of the gang starts a rock band (Electric Dream Machine), which leads indirectly to the glue-induced debut of “Dayman”, Dee and Dennis settle the debate as to whether her new rapper boyfriend Kevin is intellectually disabled. Their initial scoring system (“Retarded 2; Normal 1”) is so casually thrown into conversation, and toward the end of the episode, Kevin slams Dee with a spiteful (but beautifully-worded) rap. “I don’t think he’s retarded” is Dennis’ final say on the matter, having spent the whole episode going out of his way to ruin Dee’s relationship.

2 “The Gang Misses the Boat” (10x06)

It's Always Sunny The Gang Misses the Boat

It often goes under the radar amid the chaos of the show’s more adventurous episodes, but there’s no doubting that the entire gang is at their hilarious best in “The Gang Misses the Boat”. The second episode to focus specifically on their poor relationship with boats, the gang is late for a yacht party, and Dennis, whose general disdain for his co-workers has reached breaking point, attempts to catch up with it by driving his “amphibious exploring vehicle” right on into the ocean.

For the sake of Dennis’ sanity, Mac’s relationship with Dennis, and Frank feeling underappreciated within the group, they each decide to go their separate ways, leaving Charlie and Dee to go to lunch together. They order chicken sandwiches like normal people, enter a def poetry slam (rhyming the words “Zeus”, “shoes”, and “poops”) and even share a kiss that comes completely out of nowhere. But it makes sense that the characters who spend so little time together, and who are most regularly put down by the gang, would actually couple up nicely when left to their own devices.

Elsewhere, Dennis’ delivery of the “I am untethered and my rage knows no bounds!” speech is some of Howerton’s best ever work, while the gang finally addresses Mac’s sexuality, and Frank hops aboard another gang’s business, only to ruin it entirely. The episode works for all the characters, and at the same time makes you realize just how much these terrible, terrible people need each other.

1 “The Nightman Cometh” (4x13)

Nightman Cometh It's Always Sunny

By contrast, “The Nightman Cometh” is one of the most popular Sunny episodes, as Charlie adapts the “Dayman” teaser from “Sweet Dee’s Dating a Retarded Person” into a full-length stage musical, which devolves steadily into a disaster. Each of the gang tries to give it their own twist, with Mac bringing out the famous karate moves and Dee taking to the stage by herself to clear up the inappropriately sexual song lyrics.

The lyrics themselves, whose sinister undertones go straight over Charlie’s head, make for some of the most quotable Sunny moments. Frank turns “You gotta pay the troll toll to get into this boy’s soul” into “boy’s hole”, while Dee’s rendition of “Tiny boy, little boy – I want to touch you, boy” is equally horrific.

Charlie ends the play with a set piece of his own. Having blackmailed the Waitress into attending, he takes the moment to propose to her in front of a stunned crowd. She naturally rejects Charlie, who in turn rejects his earlier promise to stay out of her life, and the slightly awkward ending is in-keeping with the overall tone of It’s Always Sunny’s funniest all-round episode.


What did we miss? Give us your favorite It's Always Sunny in Philadelphia episodes in the comments!

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